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$111+ Cheap flights from O'Hare Intl (ORD) to Portland, ME (PWM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/22. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — PWM
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Chicago O'Hare Intl to Portland are usually found in September or March, booked 43 days in advance, depart on a Tuesday or Wednesday and return on a Thursday

Cheap flight deals from O'Hare Intl to Portland

Cheapest flights from O'Hare Intl to Portland
Explore the most affordable flight options available from O'Hare Intl to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 2025.

This American Airlines deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:54 pmORD - PWM
1 stop7h 57mAmerican Airlines
Tue 1/612:46 pmPWM - ORD
1 stop5h 04mAmerican Airlines
Deal found 12/21$294
This American Airlines deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3011:35 amORD - PWM
1 stop4h 04mAmerican Airlines
Tue 1/65:07 pmPWM - ORD
1 stop6h 27mAmerican Airlines
Deal found 12/22$299
This United Airlines deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:21 pmORD - PWM
1 stop4h 38mUnited Airlines
Fri 1/29:30 amPWM - ORD
Nonstop3h 14mUnited Airlines
Deal found 12/22$319
This United Airlines deal was found by Cheapflights users on 12/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:35 amORD - PWM
Nonstop2h 39mUnited Airlines
Tue 1/64:10 pmPWM - ORD
Nonstop3h 08mUnited Airlines
Deal found 12/21$349
This United Airlines deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3010:35 amORD - PWM
Nonstop2h 39mUnited Airlines
Sat 1/35:30 amPWM - ORD
1 stop5h 08mUnited Airlines
Deal found 12/22$364
This United Airlines deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/296:21 pmORD - PWM
1 stop4h 38mUnited Airlines
Sat 1/35:30 amPWM - ORD
1 stop5h 08mUnited Airlines
Deal found 12/22$373
This United Airlines deal was found by Cheapflights users on 12/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/255:50 pmORD - PWM
Nonstop2h 39mUnited Airlines
Thu 1/15:30 amPWM - ORD
1 stop5h 08mUnited Airlines
Deal found 12/22$379
This United Airlines deal was found by Cheapflights users on 12/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:21 pmORD - PWM
1 stop4h 38mUnited Airlines
Wed 12/317:01 pmPWM - ORD
1 stop5h 34mUnited Airlines
Deal found 12/23$389

Find flight deals from O'Hare Intl to Portland

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Portland (PWM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$209
(American Airlines)

One-way from

$111
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$441

Good round-trip deal

$305 or less

Good one-way deal

$358 or less
Provider with most accurate pricing for Chicago O'Hare Intl-Portland flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Portland flights.
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From Chicago O'Hare Intl to Portland
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One-way flight from Chicago O'Hare Intl to Portland
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Highest demand for flights based on searches. 5% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Price to beat on a round-trip flight from Chicago O'Hare Intl to Portland.
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Price to beat on a one-way flight from Chicago O'Hare Intl to Portland.
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Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 23, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Portland that are best for you.

Fly from

O'Hare Intl

Fly to

Portland

Route

Depart

Return

Price

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 6/2

6:00 pm-9:27 pm

Nonstop2h 27m

Portland

Sat 6/6

4:48 pm-6:45 pm

Nonstop2h 57m

$209

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 4/9

6:10 pm-9:40 pm

Nonstop2h 30m

Portland

Tue 4/14

7:12 pm-11:37 pm

1 stop5h 25m

$219

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 1/18

6:50 am-12:08 pm

1 stop4h 18m

Portland

Sun 1/25

5:57 pm-10:34 pm

1 stop5h 37m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 2/5

9:35 am-5:16 pm

1 stop6h 41m

Portland

Thu 2/12

6:00 am-1:23 pm

1 stop8h 23m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 6/10

6:00 am-1:21 pm

1 stop6h 21m

Portland

Sun 6/14

6:50 pm-11:55 pm

1 stop6h 05m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 3/23

9:50 am-4:06 pm

1 stop5h 16m

Portland

Sat 3/28

4:48 pm-8:14 pm

1 stop4h 26m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 6/1

6:00 pm-9:27 pm

Nonstop2h 27m

Portland

Sun 6/7

6:00 am-7:57 am

Nonstop2h 57m

$233

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 4/4

6:00 am-4:06 pm

2 stops9h 06m

Portland

Tue 4/7

4:48 pm-8:14 pm

1 stop4h 26m

$234

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 3/27

4:30 pm-10:18 pm

1 stop4h 48m

Portland

Sun 3/29

9:30 am-11:26 am

Nonstop2h 56m

$246

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 1/10

7:00 am-1:45 pm

1 stop5h 45m

Portland

Sat 1/17

2:35 pm-8:53 pm

1 stop7h 18m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 21 results
1
2
3

Compare providers for flights from O'Hare Intl to Portland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from O'Hare Intl to Portland in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Portland, Maine flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago O'Hare Intl Airport-Portland, Maine flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Portland, Maine flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Portland, Maine flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Portland, Maine flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from O'Hare Intl to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from O'Hare Intl with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago O'Hare Intl Airport to Portland

How far ahead should I book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

Use this chart to determine the optimal time to book a round-trip flight from O'Hare Intl to Portland. Price data was last updated on December 19, 2025.

To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to Portland, Maine, you should look to book at least 43 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland, Maine (average of $88). Flying from Chicago O'Hare Intl Airport to Portland, Maine in February is currently the most expensive (average of $137). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from ORD to PWM?

Find hourly flight availability from O'Hare Intl to Portland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 23, 2025.

When flying from Chicago O'Hare Intl Airport to Portland, Maine, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 14% versus a flight in the afternoon.

What is the cheapest day to fly from Chicago O'Hare Intl Airport to Portland, Maine?

Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Portland. Price data was last updated on December 20, 2025.

Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Portland, Maine flight should consider departing on Tuesday evenings when fares are most often at their lowest. Friday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated December 23, 2025.
Read through reviews of airlines operating flights from Chicago O'Hare Intl Airport to Portland, such as Delta, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,013 reviews

Crew

8.5

Comfort

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,013 reviews
Delta
7.9
Good
8,013 reviews

Crew

8.5

Comfort

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,110 reviews
Delta
7.9
Good
8,013 reviews

Crew

8.5

Comfort

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,054 reviews
Delta
7.9
Good
8,013 reviews

Crew

8.5

Comfort

7.9

Boarding

8.1

Food

7.3

Entertainment

7.9

Overall

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Portland from Chicago O'Hare Intl?

    For a flight from Chicago O'Hare Intl to Portland, you will be flying into Portland. Portland (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 4 inbound flights from Chicago O'Hare Intl per day. 3 airlines have flights to Portland from Chicago O'Hare Intl on a regular basis.

  • How long is the flight from Chicago O'Hare Intl Airport to Portland, Maine?

    Departing from Chicago O'Hare Intl Airport to Portland, Maine will take you 2h 27m. There are 897 mi between Chicago O'Hare Intl Airport and Portland, Maine. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Chicago O'Hare Intl Airport to Portland, Maine round-trip?

    According to our current data, Delta ($108), United Airlines ($218), and American Airlines ($231) offers the cheapest pricing from Chicago O'Hare Intl Airport to Portland, Maine. You may be able to fly from Chicago O'Hare Intl Airport to Portland, Maine for 71% less than the average price by searching for these airlines.

  • What are the most reliable airlines from Chicago O'Hare Intl Airport to Portland, Maine?

    The top 3 most reliable airlines when flying from Chicago O'Hare Intl Airport to Portland, Maine are Air New Zealand (79%), SkyWest Airlines (74%) and American Airlines (65%).

  • What are the cheapest flights from Chicago O'Hare Intl Airport to Portland, Maine?

    While on average a flight from Chicago O'Hare Intl Airport to Portland, Maine is generally $424, our data shows the cheapest flight currently is $195. When looking at the most popular route, (Chicago O'Hare Intl - Portland), you can expect to pay $209 for that flight.

  • Can I find deals for flights from O'Hare Intl to Portland that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Portland.

  • Can I find deals for business class flights from O'Hare Intl to Portland?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Portland, Maine (average of $88). Flying from Chicago O'Hare Intl Airport to Portland, Maine in February is currently the most expensive (average of $137). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Brunswick
Auburn
Conway

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Top 3 airlines flying from O'Hare Intl to Portland

Discover the top 3 airlines that operate flights from O'Hare Intl to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$163Average$479FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$218Average$378FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$231Average$349FlexibilityNo cancel feeOn-time71%

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